Hydrochloric Acid → Azidobenzene

Temperature

0 °C

Phenylhydrazine (6.7 g, 62 mmol) was added dropwise to a cold (0° C.) solution of concentrated hydrochloric acid (60 ml) over a period of 10 minutes. Diethyl ether (20 ml) was then added, followed by the dropwise addition of a solution of sodium nitrite (5 g, 72 mmol) in water (6 ml), keeping the temperature below 5° C. The reaction was then stirred at 0° C. for 1 hour and then extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water (2×50 ml), saturated brine (50 ml), dried (MgSO4) and carefully evaporated in vacuo to give the crude title compound as a red oil (3.3 g, 45%).

1. customthe temperature below 5° C
2. extractionextracted with ethyl acetate (3×100 ml)
3. washThe combined organic layers were washed with water (2×50 ml), saturated brine (50 ml)
4. dry with materialdried (MgSO4)
5. customcarefully evaporated in vacuo

ORD record

ord-27aff7c5f80843e59497811f9d1dfca4

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05712285